


all dolled up

by lukegodbaby



Category: IT (2017)
Genre: Crossdressing, M/M, cis male reader
Language: English
Status: Completed
Published: 2019-02-23
Updated: 2019-02-23
Packaged: 2019-11-04 04:25:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,433
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17891432
Author URL: https://archiveofourown.org/users/lukegodbaby/pseuds/lukegodbaby
Summary: you’re a guy who likes wearing dresses. and the bowers gang are guys who like that.





	all dolled up

“B-be c-c-careful,” said Bill, standing at the door of the bathroom, watching you get ready.

 

“I always am, kiddo,” you said, brushing out your long hair.

 

You knew he was right to be worried, though. You turned heads even when you weren’t all dolled up. You were tall, fine boned, with hair longer than any other guy in town. Today, you knew it would be more than that — it might even get bad. You had your favorite dress on, and that always got you dirty looks at best and shouts from strangers at worse.

 

You threw on your leather jacket to shield you from the chilly spring day, and stalked out of the house, stomping as you went and slamming the door behind you so your mom would know you were gone. She stopped talking to you when you started wearing skirts, and you couldn’t care less. If she wasn’t going to be supportive, fuck her. She ignored Bill, too, and that hurt worse than anything she failed to do for you.

 

You ended up in your favorite thrift store, run by an old hippie couple who loved your look, and encouraged you to be yourself. You loved them, and sort of wished they could be your parents.

 

“Hey, honey,” said the lady. Her name was Amethyst. “What you looking for?”

 

“A new skirt. I’ve just about worn my first one to threads,” you said.

 

She gestured you to the counter, where she pulled out a small bundle of fabric, unfolding it to show you a frankly fantastic plaid schoolgirl skirt.

 

“I think it’s your size,” she said. “Try it on for me?”

 

You grinned. “Sure, Amy.”

 

You did, and it was perfect. She seemed to always know what was going to fit you — it was even long enough to reach your knees, something almost impossible to find, as you were taller than the women these things were made for.

 

You walked out of the closet that you’d changed in, spinning for her. She clapped one hand to her mouth, her joy barely contained.

 

“I knew it would be perfect. And I can give you a deal on it, too.”

 

“You’re the best,” you said, and then went to change out of it.

 

You bought the skirt, then walked out into the sunlight shining down on the sidewalk. You were just going to head home, maybe get ice cream for Bill on your way back.

 

“Damn, baby,” said a voice behind you. “You sure look pretty all dolled up.”

 

You would have just ignored it, if it weren’t for the hand that slapped your ass as soon as the words were finished.

 

You spun around, grabbing the hand and twisting it behind the back of the boy who dared to touch you. It was Victor Criss, the bleach blonde boy who hung out with Henry Bowers and his goons. His companion, Belch Huggins, was roaring with laughter. He seemed to already know what was going on.

 

“You’re gonna want to take that back,” you said, calm as you could be.

 

“Jesus fuck,” he said. “ _Sorry_. I’m sorry, okay?”

 

You dropped his hand and he turned to look at you. His face screwed up with uncertainty as he found your face — not a girl. Not even a little bit.

 

“Sorry, man, I didn’t mean it,” he said, rubbing the arm that you’d pulled behind his back.

 

“Uh huh,” you said, crossing your arms.

 

“Really, I thought you were a chick.”

 

“I know. That doesn’t mean it was okay.”

 

“How ‘bout we make it up to you?” Belch suggested. “We’re gonna go get lunch. I’ll buy yours.”

 

“I’ll chip in,” said Vic.

 

You thought about it for a moment. These guys weren’t nice — they tormented Bill and his friends all the time. But you had nothing to do and nowhere to go, so why not? It was only lunch.

 

“Well, what the hell. Can’t say no to a free lunch. Okay.”

 

You walked with them, your dress swishing around your legs as you went, the bag with your new skirt in it by your side.

 

“Why do you even dress like that?” asked Belch.

 

“Why do you dress the way you do?” you countered.

 

“’Cause I like it.”

 

“Bingo. I like dresses.”

 

“But you look — I dunno. You look good,” said Vic. Then he blushed and tried to backtrack. “I mean, I really didn’t know you were a dude until I saw your face.”

 

“I know. Thanks, by the way.”

 

“For what?”

 

“You said I look good,” you pointed out, not going to let that drop.

 

He just blushed more and looked at his feet.

 

You all stopped in a diner and got sandwiches, the boys splitting your tab between them.

 

At one point, another customer wouldn’t stop staring at you. Belch, sitting beside you, glared the man down until he just up and left. You smiled softly down at your water.

 

“Thanks for that,” you said. “But I can handle myself, you know.”

 

“I know,” he said. Then he turned to Vic, grinning. “How’s your arm doing, by the way?”

 

Vic scowled at him. “Fine,” he grumbled.

 

You laughed, bright and loud, flipping your long hair over one shoulder as you did. You caught Vic staring at you, and you figured you had nothing to lose, so you winked at him.

 

He blushed again, staring down at his hands.

 

“You wanna hang out with us today?” he asked.

 

“I’m already hanging out with you,” you said.

 

“No, I mean all of us. We’re meeting up with Henry and Patrick soon.”

 

Your gut tightened. Henry had it out for your little brother — and the primal part of your brain was terrified of Patrick. But it was a curious thing: you were scared of him, but you also sort of wanted to crawl into his lap and never leave.

 

“I don’t know if that’s a good idea,” you said. “I’m literally wearing a dress. I don’t think they’ll dig that.”

 

You bit your lip as they thought that over.

 

Belch got out money for a tip — it was more than generous, surprising you — and shrugged.

 

“So we’ll tell them you almost kicked Vic’s ass. They’ll respect that.”

 

You thought it over. Today, it seemed, you were throwing caution to the wind, so why the hell not? Why not hang out with Henry fucking Bowers? Why not get close enough to actually end up in Patrick Hockstetter’s lap?

 

Most importantly, why not keep flirting with Vic?

 

The possibilities for the day were looking endless, and you wanted to go where they were leading you.

 

“Sure. If they don’t mind me, why not?”

 

“Cool,” said Vic, sending you a warm smile.

 

You took a chance and put your hand on top of one of his for just a moment, brushing your thumb over his knuckles before you pulled it back to your side of the table.

 

You left the diner, walking toward the library, where Vic and Belch said the others would be waiting for them, where they left the car parked.

 

As you got closer to the library, you noticed a small group of kids gathered around, and soon, you could tell it was nothing but trouble.

 

Henry fucking Bowers had your little brother in a headlock.

 

You dropped your bag and broke into a run, your boots pounding on the pavement, carrying you right up to them. You slammed an elbow into Henry’s shoulder, wrapping the other arm around Bill.

 

“That’s my fucking brother,” you growled at Henry, pulling Bill away from him, behind your back.

 

“So?” he said, advancing on you.

 

Patrick caught sight of you, his eyes traveling up and down your body, seeming to get caught on your dress, admiring your boots.

 

Vic and Belch finally arrived at the scene.

 

“Henry, he’s cool,” said Belch.

 

He had the bag with your new skirt in it tucked under one arm. Bless him.

 

“Huh?” Henry took a step back.

 

“I said, he’s cool. You don’t have to fuck with him.”

 

Henry gave you a proper once-over.

 

“He looks like a chick,” he said.

 

“Yeah, well, we thought so too. Then he nearly kicked Vic’s ass for touching him. Might be a good idea to leave his brother alone.”

 

Henry glared at you for a moment, then crossed his arms. You knew that particular battle was won.

 

You turned to Bill and his friends.

 

“You guys okay?” you asked.

 

Bill nodded instead of talking, and you knew his stutter must have gotten worse while you were apart that afternoon.

 

“Better now you turned up, sister,” said Richie, eyes bugged out behind his glasses.

 

“You get that one for free, trashmouth,” you said, sucking your teeth. “One more and I throw you back to the dogs.”

 

He looked a little deflated, so you reached out and ruffled his hair.

 

“Bev? You good?”

 

“Yeah,” she said, shaking her hair out of her eyes. “You look good as always.”

 

“Hey, I try. You guys should get out of here,” you said to the whole group.

 

“B-be c-c-c-caref-ful,” said Bill, echoing what he always said when you split ways. He glanced at Vic and Belch, and you knew that he could tell something was happening there.

 

You put a hand on his shoulder, then said, “You don’t have to worry about me, kiddo. I can take care of myself.”

 

He nodded, still looking doubtful, then turned away.

 

Mike gave you a high five, and they all left, walking their bikes away.

 

You rounded on Henry and Patrick, about to tear them a new one for picking on your kids, but Patrick spoke before you could.

 

“So, who’s this sweet little thing?” he practically purred.

 

You bared your teeth at him. “A guy,” you spat.

 

“Oh, I know, honey. But you sure look good,” he replied.

 

You willed yourself not to blush as you took a step back, and pushed part of your hair behind one ear.

 

“Thanks, I guess,” you said.

 

“You really almost kicked Vic’s ass?” asked Henry.

 

“He slapped my ass. What was I supposed to do?”

 

Henry barked out a laugh that nearly turned into a coughing fit.

 

“He slapped your ass?” asked Patrick, his eyes shining, his smile dangerous.

 

“Yeah, and he sure paid for it, didn’t ya, Vic?” said Belch, playfully shoving Vic toward you.

 

You elbowed Vic and gave him a soft smile. He looked away, the tips of his ears turning pink.

 

“Looks like someone has a crush on the pretty boy, huh, Vicky?” cooed Patrick.

 

“Hey, leave him alone. That’s our business,” you said.

 

“Oh, your business, huh? Guess you’re hard for him, too.”

 

“Maybe. What you gonna do about it?” you said, squaring up to him, planting your boots wide.

 

“Nothing. Watch, maybe.” He grinned at you, and your stomach flipped over.

 

“I’m bored of talking,” said Henry. “Let’s get the fuck out of here. Belch?”

 

Belch nodded, pulling his keys out of his pocket.

 

You all piled into the Trans Am, you ending up pressed in between Patrick and Vic. Patrick slung an arm around your shoulders and you wanted to both pull away and press yourself closer to him.

 

You did neither, simply putting your hand on Vic’s knee. He looked at you, eyes wide, then looked away like he didn’t know what to do.

 

You smiled, then leaned into him. He froze, then made a concentrated effort to relax into you.

 

“You look good,” said Henry, glancing back at you as you drove past the town’s square.

 

“Thanks, man,” you said.

 

“No, I mean, real good. Not just good. You look hot.”

 

You reeled for a second, then looked closely at his face. He meant it — he wasn’t fucking with you.

 

“Thanks,” you said, your voice soft.

 

You didn’t know what else to say. Guys usually didn’t like the way you looked, which sucked, seeing as you were firmly in the camp of liking guys.

 

Vic put his hand on top of yours, then said, quietly, “can I kiss you?”

 

You smiled gently at him, then nodded.

 

He kissed you, a softer thing than you’d ever expected to come out of any of these boys.

 

You turned to be able to kiss him better, full-on, and you felt Patrick’s hands close in around your hips, one hand trailing down your leg, pulling up the skirt of your dress.

 

You broke the kiss to look back at Patrick, a question on your face. It sounded a little like _what the hell._ He shrugged.

 

“You didn’t think Vic was the only one with a thing for a guy in a dress, did you?” he asked, giving you that shark-faced grin.

 

Your stomach flipped again, and you put your hand on top of his, slowly sliding it up and down your leg, pushing the skirt up a little higher with every pass, looking him dead in the eye as you did.

 

“Good boy,” he breathed in your ear.

 

You shivered. He nosed at your neck, pulling your hair to the side to breathe you in.

 

You turned to kiss Vic again, and he put so much more energy into it, maybe to get your attention back from Patrick, but maybe because he wasn’t feeling shy anymore. He took your face between his hands and held you still while he slid his tongue into your mouth. You moaned around it, slinging your arms over his shoulders, wanting to get in his lap.

 

He seemed to read your mind, hauling you on top of him, moving in closer to Patrick so he could still touch you.

 

Henry and Belch talked quietly up front, and you couldn’t really hear what they were saying, but you thought they were deciding where to go.

 

Sure enough, a minute later, they pulled into the driveway of a small house.

 

You broke away from kissing Vic, breathing hard.

 

“Where are we?” you asked.

 

“Belch’s place,” he answered, pushing your hair out of your face. “You wanna go in?”

 

“Sure,” you said. Then, you took Patrick’s hand off you, pulling your dress back down.

 

He groaned. “But we were finally getting somewhere,” he said.

 

“If you wanna get farther, I’d prefer it not be in a car,” you said. “There’s not enough room for everyone.”

 

Then you had to pause, realizing that yes, everyone. You were interested in all of the boys.

 

“Just as long as I get to take that dress off you, I don’t care where we are. Now let’s go,” said Henry, climbing out of the car.

 

You followed, ready for the ride of your life.

**Author's Note:**

> catch me on tumblr at god--baby.tumblr.com


End file.
